69936-03-4Relevant articles and documents
Rhodium(III)-Catalyzed C-H Alkenylation: Access to Maleimide-Decorated Tryptophan and Tryptophan-Containing Peptides
Khamrakulov, Mirzadavlat,Li, Chunpu,Liu, Hong,Peng, Jingjing,Wang, Jiang
supporting information, p. 1535 - 1541 (2020/03/13)
Maleimide is widely applied in many fields, especially in antibody-drug conjugations and peptide drugs. Herein, we develop a strategy for the C-H alkenylation of tryptophan and tryptophan-containing peptides, providing a synthetic route of decorating male
Heteroatom-Interchanged Isomers of Lissoclinamide 5: Copper(II) Complexation, Halide Binding, and Biological Activity
Xie, Sida,Savchenko, Andrei I.,Kerscher, Marion,Grange, Rebecca L.,Krenske, Elizabeth H.,Harmer, Jeffrey R.,Bauer, Michelle J.,Broit, Natasa,Watters, Dianne J.,Boyle, Glen M.,Bernhardt, Paul V.,Parsons, Peter G.,Comba, Peter,Gahan, Lawrence R.,Williams, Craig M.
, p. 1465 - 1476 (2018/04/06)
Cyclic peptides, especially those produced by marine cyanobacteria symbionts, are considered to play an important ecological role in host defence. Chemists have long compared the cyclic peptide cavitand architecture with that of macrocyclic ligands, and proposed that they mediate metal-ion transport. The study presented herein investigated the metal chelation of non-natural heteroatom-interchanged (HI) isomers of lissoclinamide 5, by using MS, EPR, and DFT calculations. The latter identified three possible structures for the CuII complex with natural lissoclinamide 5, with the most likely determined to be that with the metal ion bound through the nitrogen donors of the thiazoles and one deprotonated amide. For HI-lissoclinamide 5 the calculations suggest that the CuII ion is bound in a bidentate manner by the oxazoline nitrogen atom and one deprotonated amide nitrogen atom, with the S donor of the thiazole not involved in coordination. Along with evidence of copper binding these systems also bound halide ions. Evaluation of the anti-cancer properties demonstrated that the biological activity of HI-lissoclinamide 5 against T24 bladder cells was eleven-fold lower as compared to natural lissoclinamide 5. Addition of a CuII salt had no effect on the activity of lissoclinamide 5. Overall, this comprehensive study of the HI concept has demonstrated that small changes propagate dramatic effects in complexation, halide binding, and biological activity.
Synthesis of 3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Gaidukevich,Rudenkova,Popova,Nikolaevich,Knizhnikov
, p. 1562 - 1564 (2019/01/04)
3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione [cyclo(Pro-Phe)] was synthesized by cyclization of prolylphenylalanine and phenylalanylproline methyl esters which were prepared from the corresponding Boc-protected amino acids.
Synthesis of Cyclic Peptidomimetics via a Pd-Catalyzed Macroamination Reaction
Hopkins, Brett A.,Smith, Graham F.,Sciammetta, Nunzio
, p. 4072 - 4075 (2016/08/30)
A new method to access cyclic peptidomimetics via a Pd-catalyzed macroamination reaction is presented. Natural amino acid amines are revealed as proficient coupling partners in these transformations. With a commercially available CPhos G3 catalyst system and substrates bearing diverse amino acid and aryl halide backbones, the unique head to side-chain (or side-chain mimic) macrocycles are afforded with ring sizes from 11 to 23 members in yields up to 84%.
Efficient construction of proline-containing β-turn mimetic cyclic tetrapeptides via CuAAC macrocyclization
Chouhan, Gagan,James, Keith
, p. 1206 - 1209 (2013/05/21)
A range of macrocyclic β-turn mimetic tetrapeptides was prepared by efficient copper-tris(triazole) ligand complex catalyzed azide-alkyne "click" macrocyclizations in good to high yields. Preliminary conformational studies using X-ray crystallography and NMR spectroscopy demonstrated the presence of intramolecular H-bonds characteristic of β-turns in these cyclic tetrapeptides.
Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin
Yokokawa, Fumiaki,Sameshima, Hirofumi,In, Yasuko,Minoura, Katsuhiko,Ishida, Toshimasa,Shioiri, Takayuki
, p. 8127 - 8143 (2007/10/03)
The first total synthesis of cis,cis-ceratospongamide (cyclo[L-Pro-L-Ile-Me-oxazoline-L-Phe-L-Pro-thiazole-L-Phe-]) was accomplished and confirmed by X-ray crystal analysis. The heating of cis,cis-ceratospongamide in DMSO converted it not to the trans,trans isomer but to the trans,trans-[D-allo-Ile]-ceratospongamide, which was confirmed by total synthesis. Its solution conformation was constructed by the dynamic simulated annealing method using ROE cross peaks, revealing a rounded and flat ring structure which is in contrast with the slim and tight structure of cis,cis isomer. The results shows that the trans,trans-[D-allo-Ile] isomer is the main thermal product of cis,cis-ceratospongamide.
A Cyclic Analogue of Hexapeptide Tyr-Val-Pro-Leu-Phe-Pro, A Peptide Immunostimulant
Siemion, I. Z.,Szewczuk, Z.,Lisowski, M.
, p. 877 - 883 (2007/10/02)
A cyclic analogue of the peptide immunoeffector, hexapeptide Tyr-Val-Pro-Leu-Phe-Pro, was synthesized by different methods in solution.A comparison of the BOP reagent with the classical p-nitrophenyl ester method for the cyclization reaction shows that in
